title: Nickel-catalyzed arylation, alkenylation, and alkynylation of unprotected thioglycosides at room temperature.
abstract: Unprotected thioglycosides were effective nucleophiles for Ni(0)-catalyzed C-S bond-forming reaction with functionalized (hetero)aryl, alkenyl, and alkynyl halides. The functional-group tolerance on the electrophilic partner was typically high and the anomeric selectivities of the thioglycosides were high in all cases. The efficiency of this general procedure was well-demonstrated by the synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB).
authors.affiliation: Laboratoire de Chimie Thérapeutique, BioCIS-UMR 8076, LabEx LERMIT, Université Paris-Sud, CNRS, Faculté de Pharmacie, 5 rue J.-B. Clément, 92296 Châtenay-Malabry (France), Fax: (+33)146-83-58-28.
authors.forename: Etienne
authors.initials: E
authors.lastname: Brachet
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.forename: Mouad
authors.initials: M
authors.lastname: Alami
authors.forename: Samir
authors.initials: S
authors.lastname: Messaoudi
mesh_terms: D002384:Catalysis; D009532:Nickel / Q000737:chemistry*; D013696:Temperature; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D013865:Thioglycosides; D009532:Nickel
keywords: alkenylation; alkynylation; arylation; nickel; thioglycosides